Cefalotin

Cefalotin
Clinical data
AHFS/Drugs.com	International Drug Names
MedlinePlus	a682860
Pregnancy; category	AU: A; ;
Routes of; administration	Intravenous
ATC code	J01DB03 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); UK: POM (Prescription only);
Pharmacokinetic data
Bioavailability	n/a
Protein binding	65 to 80%
Metabolism	Hepatic
Elimination half-life	30 minutes to 1 hour
Excretion	Renal
Identifiers
	IUPAC name (6R,7R)-3-[(acetoxy)methyl]-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;
CAS Number	153-61-7 ;
PubChem CID	6024;
DrugBank	DB00456 ;
ChemSpider	5802 ;
UNII	R72LW146E6;
KEGG	D07635 ;
ChEBI	CHEBI:124991 ;
ChEMBL	ChEMBL617 ;
CompTox Dashboard (EPA)	DTXSID4022783 ;
ECHA InfoCard	100.005.288
Chemical and physical data
Formula	C16H16N2O6S2
Molar mass	396.43 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	160 to 160.5 °C (320.0 to 320.9 °F)
	SMILES O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)Cc3sccc3)COC(=O)C)C(=O)O;
	InChI InChI=1S/C16H16N2O6S2/c1-8(19)24-6-9-7-26-15-12(14(21)18(15)13(9)16(22)23)17-11(20)5-10-3-2-4-25-10/h2-4,12,15H,5-7H2,1H3,(H,17,20)(H,22,23)/t12-,15-/m1/s1 ; Key:XIURVHNZVLADCM-IUODEOHRSA-N ;
	(verify)

Cefalotin (INN) /ˌsɛfəˈloʊtɪn/ or cephalothin (USAN) /ˌsɛfəˈloʊθɪn/ is a first-generation cephalosporin antibiotic with broad spectrum antibiotic activity.^[1]^[2] It was the first cephalosporin marketed (1964) and continues to be widely used.^[3] Cefalotin is used for bacterial infections of the respiratory tract, urinary tract, skin, soft tissues, bones and joints, sepsis, peritonitis, osteomyelitis, mastitis, infected wounds, and post-operational infections.^[2]

It is an intravenously administered agent with a similar antimicrobial spectrum to cefazolin and the oral agents cefalexin and cefadroxil. Cefalotin sodium is marketed as Keflin (Lilly) and under other trade names.^[4]

The compound is a derivative of thiophene-2-acetic acid.^[5]

References

^ Hameed TK, Robinson JL (July 2002). "Review of the use of cephalosporins in children with anaphylactic reactions from penicillins". The Canadian Journal of Infectious Diseases. 13 (4): 253–8. doi:10.1155/2002/712594. PMC 2094874. PMID 18159398.
^ ^a ^b Vardanyan R, Hruby V (2006). "Antibiotics". Synthesis of Essential Drugs. pp. 425–498. doi:10.1016/B978-044452166-8/50032-7. ISBN 978-0-444-52166-8.
^ Greenwood D (21 February 2008). Antimicrobial Drugs: Chronicle of a Twentieth Century Medical Triumph. OUP Oxford. pp. 128–. ISBN 978-0-19-953484-5.
^ International Drug Names: Cefalotin
^ Swanston J (2006). "Thiophene". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_793.pub2. ISBN 3527306730..

[1] Hameed TK, Robinson JL (July 2002). "Review of the use of cephalosporins in children with anaphylactic reactions from penicillins". The Canadian Journal of Infectious Diseases. 13 (4): 253–8. doi:10.1155/2002/712594. PMC 2094874. PMID 18159398.

[Vardanyan_2006-2] Vardanyan R, Hruby V (2006). "Antibiotics". Synthesis of Essential Drugs. pp. 425–498. doi:10.1016/B978-044452166-8/50032-7. ISBN 978-0-444-52166-8.

[Greenwood2008-3] Greenwood D (21 February 2008). Antimicrobial Drugs: Chronicle of a Twentieth Century Medical Triumph. OUP Oxford. pp. 128–. ISBN 978-0-19-953484-5.

[4] International Drug Names: Cefalotin

[Ullmann-5] Swanston J (2006). "Thiophene". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_793.pub2. ISBN 3527306730..

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